Synthesis, biological activities, and SAR studies of novel 1-(2-chloro-4, 5-difluorophenyl)-1H-pyrazole derivatives. Issue 22 (15th November 2020)

• Record Type: Journal Article
• Authors: Zhao, Yangyang; Li, Huangong; Sun, Pengwei; Gao, Li; Liu, Jingbo; Zhou, Sha; Xiong, Lixia; Yang, Na; Li, Yuxin; Li, Zhengming
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 30:Issue 22(2020)
• Publication Date: 2020-11-15
• Subjects: 1-(2-Chloro-4, 5-difluorophenyl)-1H-pyrazole -- Modified pyrazole -- Insecticidal activity -- SAR -- Electrophysiology study -- Anthranilic diamide; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2020.127535
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Highlights: Novel fluoro-substituted anthranilic diamides derivatives were designed and synthesized. IVc showed excellent larvicidal activities against Mythimna separata and P. xylostella . The ether groups played an important role in the larvicidal activity. Ryanodine receptor was the potential biochemical target of these compounds. Abstract: In order to search for the new ryanodine receptor (RyR) regulator, a series of 35 novel fluoro-substituted compounds introduced 1-(2-chloro-4, 5-difluorophenyl)-1 H -pyrazole moiety containing modified pyrazole heterocycle were designed and synthesized. Then, they were tested for the insecticidal activities against Mythimna separata and Plutella xylostella in our greenhouse. After a systematic biological screening, it was found out that IVc showed 50% larvicidal activities against Mythimna separata at 0.1 mg L −1, equivalent to that of chlorantraniliprole (36%, 0.1 mg L −1 ). The activity of IVc against Plutella xylostella was 90% at 10 −5 mg L −1, whereas the chlorantraniliprole was 70% at the same concentration. Then, insect electrophysiology experiments were conducted to study the pattern of action of IVc and IVe . It was confirmed by the experimental results that both compounds could lead to the release of calcium from the endoplasmic reticulum of neurons as classical anthranilic diamide insecticides.